3-{1-[4-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-3-hydroxymethyl-butyryl]-piperidin-4-yl}1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one → 2-(4-Amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyraldehyde
Reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH2:12][CH:13]([CH2:35][OH:36])[CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[CH2:29][CH2:28][C:27]4[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=4[NH:25][C:24]3=[O:34])[CH2:19][CH2:18]2)=[O:16])=[CH:4][C:3]=1[Cl:37]>ClCCl>[NH2:1][C:2]1[C:7]([C:8]([F:10])([F:9])[F:11])=[CH:6][C:5]([CH2:12][CH:13]([CH2:14][C:15](=[O:16])[N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[CH2:29][CH2:28][C:27]4[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=4[NH:25][C:24]3=[O:34])[CH2:21][CH2:22]2)[CH:35]=[O:36])=[CH:4][C:3]=1[Cl:37]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 0.539 g (1.000 mmol) 3-{1-[4-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-3-hydroxymethyl-butyryl]-piperidin-4-yl}1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one (Intermediate product 35) in 10 mL dichloromethane was added 0.933 g (2.200 mmol) Dess-Martin-Periodinane and the mixture was stirred for 3 hours at RT. The reaction mixture was washed with sat. aqueous sodium thiosulphate solution and sat. aqueous NaCl solution, dried over sodium sulphate and evaporated down i. vac. The crude product was purified by column chromatography (silica gel, gradient dichloromethane/MeOH 50:1→25:1 v/v).